CAS Number23109-05-9
Synonymsalpha-amanitin; MFCD00215842; EINECS 245-432-2; A-AMANITIN; AMANITIN,A
Molecular FormulaC39H54N10O14S
Molecular Weight918.97000
Purity90%
Density1.57 g/cm3
Boiling Point1622.2ºC at 760 mmHg
Melting Point254-255ºC(lit.)
Appearancewhite to light yellow
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 23109-05-9 |
| Catalog No. | 2A-9060813 |
| Chinese Name | Α-毒伞肽 |
| Synonyms | alpha-amanitin; MFCD00215842; EINECS 245-432-2; A-AMANITIN; AMANITIN,A |
| Molecular Formula | C39H54N10O14S |
| Molecular Weight | 918.97000 |
| Purity | 90 |
| Density | 1.57 g/cm3 |
| Boiling Point | 1622.2ºC at 760 mmHg |
| Melting Point | 254-255ºC(lit.) |
| Appearance | white to light yellow |
| Storage Condition | -20℃ |
| Packaging | I |
| Application | Alpha-Amanitin is the main toxin of several deadly poisonous mushrooms and exerts its toxic effects by inhibiting RNA polymerase II. |
| SMILES | CCC(C)C1NC(=O)CNC(=O)C2Cc3c([nH]c4cc(O)ccc34)S(=O)CC(NC(=O)CNC1=O)C(=O)NC(CC(N)=O)C(=O)N1CC(O)CC1C(=O)NC(C(C)C(O)CO)C(=O)N2 |
| InChI | InChI=1S/C39H54N10O14S/c1-4-16(2)31-36(60)42-11-29(55)43-25-15-64(63)38-21(20-6-5-18(51)7-22(20)46-38)9-23(33(57)41-12-30(56)47-31)44-37(61)32(17(3)27(53)14-50)48-35(59)26-8-19(52)13-49(26)39(62)24(10-28(40)54)45-34(25)58/h5-7,16-17,19,23-27,31-32,46,50-53H,4,8-15H2,1-3H3,(H2,40,54)(H,41,57)(H,42,60)(H,43,55)(H,44,61)(H,45,58)(H,47,56)(H,48,59) |
| InChI Key | CIORWBWIBBPXCG-NUCBJAHASA-N |
| Hazard Symbols | 6.1(a) |
| Bioactivity | alpha-Amanitin is the principal toxin of several deadly poisonous mushrooms, exerting its toxic function by inhibiting RNA-polymerase II. Related Catalog Signaling Pathways >> Antibody-drug Conjugate >> ADC Cytotoxin Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis Research Areas >> Cancer Target ADCs cytotoxin, RNA-polymerase II[1] In Vitro Alpha-Amanitin decreases TAF15 mRNA and TAF15 protein levels in MKN45 cells, and inhibits the RNAPII activity towards TAF15 mRNA[2]. alpha-Amanitin decreases cell viability by 14%, 21%, 41%, 44%, and 50% at concentrations of 100, 10, 1, 0.1, and 0.01 µg/mL, respectively. The LD50 of the alpha-Amanitin at 36 h is measured as 1 µg/mL. The total amount of protein within the cell at 24 h is significantly increased for the 1 µg/mL dose of alpha-Amanitin compared to the control[3]. Alpha-Amanitin dramatically decreases the expression of gap junctional genes (Gja1, Gja4 and Gjc1) and gonadotropin receptor genes (FSHr and LHr) in cumulus cells[4]. In Vivo The intravenous LD50 dose of alpha-Amanitin is 0.327 mg/kg body weight after intravenous injection into BALB/c mice. After 12 h of alpha-Amanitin injection in caudal vein, the levels of WBC, RBC and HGB decrease significantly, while those of BUN and Crea increase significantly in serum. alpha-Amanitin inhibits some genes (Hsp90b1, Irx4, etc.), whose encoded proteins regulate the RNA polymerase II activity. alpha-Amanitin down-regulates some proteins (Nmi, Trpc5, etc.) taking part in the transcription progress[1]. alpha-Amanitin has potent activity in DTC suppression. Mice injected with alpha-Amanitin (0.4 mg/kg, i.p.)-treated cells maintain their body weight, while those receiving a peritoneal injection of MKN45 cells show a constant decrease in body weight[2]. Cell Assay The MTT assay is used to evaluate the overall functional integrity and viability of the cultured cells. The MCF-7 cells are put into 96-well plates (2×104 for each well), which are incubated for 24 h. The specific concentrations of alpha-Amanitin and β-Amanitin are added to the cell culture medium, and plates are incubated for an additional 36 h. MTT solution (1:10 ratio) and dimethyl sulfoxide (DMSO) (100 µL) are then added to the cell culture medium and plates are incubated overnight. The absorbance is measured at 570 nm on a plate reader. This experiment is repeated 3 times. The absorbance data are calculated as percentages according to the control group. Animal Admin For tumorigenicity tests, six colonies (untreated) and DTCs derived from MKN45 cells are individually injected subcutaneously into the left and right side of the backs of six 6-week-old female nude mice (BALB/cAjcl-nu/nu). These mice are monitored for 49 days after the inoculation or until tumors reach 10 mm in the largest diameter, and are then euthanized. For the PC model, 1.0×106 MKN45 cells are injected intraperitoneally into six 6-week-old female nude mice (BALB/cAjcl-nu/nu). Mice are then treated with CIS (4.0 mg/kg, intraperitoneal administration) or a combination of CIS and alpha-Amanitin (0.4 mg/kg, intraperitoneal administration). For the combination treatment, alpha-Amanitin is given 24 hours before CIS. Body weight is monitored for 28 days after the treatment. References [1]. Zhao J, et al. Pathological effects of the mushroom toxin alpha-amanitin on BALB/c mice. Peptides. 2006 Dec;27(12):3047-3052. [2]. Kume K, et al. α-Amanitin Restrains Cancer Relapse from Drug-Tolerant Cell Subpopulations via TAF15. Sci Rep. 2016 May 16;6:25895 [3]. Kaya E, et al. Evaluation and comparison of alpha- and beta-amanitin toxicity on MCF-7 cell line. Turk J Med Sci. 2014;44(5):728-32 [4]. Park MW, et al. RNA Polymerase II Inhibitor, α-Amanitin, Affects Gene Expression for Gap Junctions and Metabolic Capabilities of Cumulus Cells, but Not Oocyte, during in vitro Mouse Oocyte Maturation. Dev Reprod. 2013 Mar;17(1):63-72 Chemical & Physical Properties Density 1.57 g/cm3 Boiling Point 1622.2ºC at 760 mmHg Melting Point 254-255ºC(lit.) Molecular Formula C39H54N10O14S Molecular Weight 918.97000 Flash Point 934.9ºC Exact Mass 918.35400 PSA 400.09000 Index of Refraction 1.694 InChIKey CIORWBWIBBPXCG-NUCBJAHASA-N SMILES CCC(C)C1NC(=O)CNC(=O)C2Cc3c([nH]c4cc(O)ccc34)S(=O)CC(NC(=O)CNC1=O)C(=O)NC(CC(N)=O)C(=O)N1CC(O)CC1C(=O)NC(C(C)C(O)CO)C(=O)N2 |
| Use of | alpha-Amanitin is the principal toxin of several deadly poisonous mushrooms, exerting its toxic function by inhibiting RNA-polymerase II. Properties Articles13 Name α-amanitin Synonym More Synonyms alpha-Amanitin Biological Activity Description alpha-Amanitin is the principal toxin of several deadly poisonous mushrooms, exerting its toxic function by inhibiting RNA-polymerase II. Related Catalog Signaling Pathways >> Antibody-drug Conjugate >> ADC Cytotoxin Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis Research Areas >> Cancer ADCs cytotoxin, RNA-polymerase II[1] References [1]. Zhao J, et al. Pathological effects of the mushroom toxin alpha-amanitin on BALB/c mice. Peptides. 2006 Dec;27(12):3047-3052. [2]. Kume K, et al. α-Amanitin Restrains Cancer Relapse from Drug-Tolerant Cell Subpopulations via TAF15. Sci Rep. 2016 May 16;6:25895 [4]. Park MW, et al. RNA Polymerase II Inhibitor, α-Amanitin, Affects Gene Expression for Gap Junctions and Metabolic Capabilities of Cumulus Cells, but Not Oocyte, during in vitro Mouse Oocyte Maturation. Dev Reprod. 2013 Mar;17(1):63-72 Chemical & Physical Properties Molecular Formula C39H54N10O14S Exact Mass 918.35400 PSA 400.09000 Index of Refraction 1.694 InChIKey CIORWBWIBBPXCG-NUCBJAHASA-N |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Danger Regulations: 3462 International Maritime Transport Danger Regulations: 3462 International Air Transport Danger Regulations: 3462 14.2 United Nations shipping name European Land Transport Dangerous Regulations: TOXINS EXTRACTED FROM LIVING SOURCES, SOLID, N.O.S. (α-Amanitin) IMDG Code: TOXINS, EXTRACTED FROM LIVING SOURCES, SOLID, N.O.S. (α-Amanitin) International Air Transport Risk Regulations: Toxins, extracted from living sources, solid, n.o.s. (α-Amanitin) 14.3 Transport hazard categories European Land Transport Danger Regulations: 6.1 International Maritime Transport Danger Regulations: 6.1 International Air Transport Danger Regulations: 6.1 14.4 Package group European Dangerous Regulations for land transport: II International Dangerous Regulations for sea transport: II International Dangerous Regulations for air transport: II 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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